تفاعل #91313

معادلة التفاعل

Methyl 3-bromoisonicotinate

4-fluorobenzylamine

Xantphos

cesium carbonate

→

title compound

المردود 88.0%

methyl 3-[(4-fluorobenzyl)amino]pyridine-4-carboxylate

المردود 88.0%

المذيبات

dioxane

ظروف التفاعل

المعالجة

1. 1
   ترشيحThe mixture was then filtered
2. 2
   غسيلwashing with DCM
3. 3
   أخرىto remove solids
4. 4
   تركيزThe solution was concentrated in vacuo
5. 5
   أخرىpurified by silica gel chromatography (20-50% EtOAc/hexanes)

الإجراء التجريبي

Methyl 3-bromoisonicotinate (220 mg, 1.02 mmol), 4-fluorobenzylamine (132 μL, 1.22 mmol), tris(dibenzylideneacetone)dipalladium(0) (47 mg, 0.051 mmol), Xantphos (89 mg, 0.153 mmol), and cesium carbonate (500 mg, 1.53 mmol) were combined in dioxane (4 mL) under N2 in a sealed microwave tube. The reaction mixture was heated at 116° C. in a microwave for 1 h. The mixture was then filtered, washing with DCM, to remove solids. The solution was concentrated in vacuo and purified by silica gel chromatography (20-50% EtOAc/hexanes) to give 228 mg (88%) of the title compound as a white solid. 1H NMR (400 MHz, CDCl3): δ 8.18 (s, 1H), 7.93 (d, 1H, J=5.0 Hz), 7.79 (br s, 1H), 7.63 (d, 1H, J=5.0 Hz), 7.27-7.34 (m, 2H), 7.03 (t, 2H, J=8.6 Hz), 4.47 (d, 2H, J=5.6 Hz), 3.89 (s, 3H). [M+H] calc'd for C14H13FN2O2, 261. found 261.

المصدر